Showing papers in "Journal of Carbohydrate Chemistry in 2005"

TL;DR: Iodine-promoted glycosylation of serine and threonine with 2‐azido‐2‐deoxy‐glycosyl iodides, easily obtained in three steps, proceeded smoothly, resulting in only α‐linked products in high yield in most cases.

TL;DR: MacDowell as mentioned in this paper used a palladium-catalyzed glycosylation reaction to synthesize 1,1,α,manno-disaccharides from acylfurans.

TL;DR: The activation of 2‐azido‐2‐deoxy Tn and TF thioglycosyl donors by the powerful thiophilic promoter system Ph2SO/Tf2O has been investigated and glycosylation of an Fmoc‐protected threonine derivative gave 1,2‐cis glycosides in high yields and excellent stereoselectivities.

TL;DR: The synthesis of new pseudo‐C‐nucleosides was accomplished starting from 3‐O‐benzyl‐1,2‐O-isopropylidene‐α‐D‐ribo‐pentodialdo‐1‐4‐furanose, aiming to build thiazole, triazole, tetrazole, and thiazolidinone derivatives, finding selective activity may indicate potential application of these structures for amelioration of Alzheimer's disease

TL;DR: It is demonstrated that 1,N-Dicyclohexyl benzenesulfinamide does not activate thioglycosides in combination with trifluoromethanesulfonic anhydride, which is attributed to its greater steric bulk.

TL;DR: A thioglycoside aminotriol scaffold has been elaborated by acylation, reductive alkylation, sulfonation, phosphorylation, and other procedures to produce a library of 40 functionalized thiglycosides that superficially resemble the enzyme‐binding portions of the Mycobacterium tuberculosis detoxifier mycothiol and its metabolic congeners.

TL;DR: An efficient one-pot protocol for the direct preparation of thioglycosides starting from unprotected reducing sugars via S−glycosyl isothiouronium salts is reported in this article.

TL;DR: The use of neomycin isothiocyanate as an electrophilic reagent for a general route to aminoglycoside‐coupled nucleic acid biopolymers is described.

TL;DR: In this article, the synthesis of 2,3,4,6,6-tetra derivatives of 2.5-acetyl β,β,β-1-thiotrehalose were presented.

TL;DR: Synthesis of a thioglycoside tetrasaccharide block, corresponding to the repeating unit of Streptococcus pneumoniae serotype 14 CPS, yields an octa and a dodecasaccharides derivative ready for conjugation to proteins to afford immunoactive glycoconjugates.

TL;DR: In this paper, short synthetic routes to protected ethyl 2−deoxy−2−phthalimido−1−β−D−thio−galactosamine derivatives via epimerization of the corresponding glucosamine compounds are described.

TL;DR: The generality and value of this procedure have been demonstrated by the preparation of peracetylated Gb3, GM2, and fucosyl GM1 glycosylamino acids, which are of potentially large value in the Preparation of future anticancer vaccines.

TL;DR: The α and β acetylated (5−formyl−2−furyl)methyl-Dglucopyranosides were synthesized and converted into acetyl-ated ranunculin diastereoisomers and δ−glucosyloxy-γ-oxo esters.

TL;DR: In this paper, chitosan was hydrophobized by esterification reaction with acyl chlorides; its derivatives were swelling in water and characterized by 13C and 1H NMR and infrared spectroscopy.

TL;DR: Despite significant progress in the area of synthetic carbohydrate chemistry, the necessity to form a glycosidic bond with complete stereoselectivity remains to be the main reason chemical O-glycosylation is still ranked among the most challenging problems of modern synthetic chemistry.

TL;DR: In the glycosylation of primers by cells, this research confirmed that sialyl transferases tolerate acceptor modifications and are permissive to primer elongation regardless of the α‐ or β‐linkage to the aglycon unit.

TL;DR: In this article, the conformational behavior of linear (1→3)linked propyl di−, tri−, tetrafucosides and 2,3-branched tetraffusides with linear trisaccharide backbone related to fragments of natural fucoidans was studied by theoretical molecular modeling and experimental determination of transglycosidic vicinal coupling constants 3JC,H.

TL;DR: An effective new preparative synthesis of the conserved linear pseudopentasaccharide structure of the GPI anchors and of the full GPI structure has been carried out that has permitted obtaining both molecules in sufficient quantities as to perform further structural and biologic studies.

TL;DR: Stiles as discussed by the authors synthesized S−Glycosyl L−aspartic acid building blocks starting from 1−thiosugars by reaction with 5−aminopentanol and suitably protected L−ASPIC acid pentafluorophenyl ester in a one-pot procedure under Mitsunobu conditions using 1,1′−azodicarbonyl dipiperidine and trimethyl phosphine.

TL;DR: In this paper, the advantages, disadvantages, and anomalies of various donors in glycosidations are discussed, and it is shown that regiopreferences are not very sensitive to the type of donor used.

TL;DR: In this paper, the synthesis and characterization of hydrophobic derivatives of dextran in which long alkyl chains substituted a proportion of the hydroxyl groups was reported.

TL;DR: A short and time‐efficient route was applied for the synthesis of N‐glycosylated amino acid building blocks in good overall yields by coupling unprotected glycosylamines and N α‐Fmoc‐Asp(OH)‐O t Bu using TBTU activation.

TL;DR: Balasubramanian et al. as mentioned in this paper synthesize mimetics of the widely distributed GlcNAc•Asn linkage in glycoproteins in four steps involving selective N•chloroacetylation, peracetylization catalyzed by Na β−zeolite, displacement of the Cl group by NaN3 in aqueous acetone, and Zemplen de−O•acetylations.

TL;DR: In this paper, an efficient and selective cross-metathesis (CM) of both α and β anomers of C−allyl−glucose and N−acetyl−C‐allyl•glucosamine with electron-deficient olefins is reported.

TL;DR: The enzyme activity transferring a β‐primeverosyl unit was found from culture filtrates of Penicillium multicolor IAM7153 and was useful for synthesizing a series of β‐ primeverosides via aβ‐prime Verosyl transfer reaction in an aqueous‐organic biphasic system.

TL;DR: An array of synthons is required to access an oligosaccharide library; however, multistep and thus time‐consuming synthesis is inevitable, so multiple benzyl groups were successfully incorporated in one step.

TL;DR: In this paper, a new protocol was developed for the generation of alkylidenecarbene derivatives of monosaccharides based on the reaction of trimethylsilylazide and Bu2SnO with α-cyanomesylates derived from uloses.

TL;DR: The first synthesis of 3.O.β.D.glucopyranosyl (3R)•hydroxybutanolide (Kinsenoside) was described in this article.

TL;DR: The chemistry of saccharides has emerged as a new sub-area of pharmaceuticals as discussed by the authors and a new series of chiral complexes have been isolated and characterized Molar conductance measurements show that the complexes are ionic, and the spectral data are indicative of octahedral geometry of the complexes.

TL;DR: Some attempts toward the synthesis of novel inhibitors of glycosyl transferases are described and none of these three novel compounds proved to be a significant inhibitor of a retaining α‐glucosidase from barley.